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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-07-29 21:31:02 UTC
Secondary Accession Numbers
  • HMDB00975
Metabolite Identification
Common NameTrehalose
DescriptionTrehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID: 12105274 ; PMID: 25479689 ) (
Ergot sugarChEBI
Natural trehaloseHMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranosideHMDB
Α-D-glucopyranosyl α-D-glucopyranosideHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
Traditional Nameα,α'-trehalose
CAS Registry Number99-20-7
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility592 g/LALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.14 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-b710c7c4bd86fd5f1af0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-2e5f22e6ba282283a569Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9832000000-b3259de2e25ea7293565Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wos-0921000000-68fb82f427417ec703a0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0943000000-07c11d483e4278dc639aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-8932000000-c327fe31b8d3e86dd97dSpectrum
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0j4l-0954000000-33e230d28780be607983Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-b710c7c4bd86fd5f1af0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-2e5f22e6ba282283a569Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9832000000-b3259de2e25ea7293565Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wos-0921000000-68fb82f427417ec703a0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0943000000-07c11d483e4278dc639aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8932000000-c327fe31b8d3e86dd97dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0j4l-0954000000-33e230d28780be607983Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i2d-0921000000-9e633378baf1645df2a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ni-9554000000-e418bec346785e269084Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2553419000-dd0bea0ade3ee46308dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1901000000-865e9e390fac7d13c2f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9500000000-7d4c9de285c2872d2320Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c71f25d08b875caff6b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-0019000000-3b4e276ff5686c841bddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-8905000000-fafde7828ce0d63fe618Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-d382926500274fb84a46Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-10524d7a715f8a0ed265Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0019000000-3b4e276ff5686c841bddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-8981579ae1dd58ba65c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-4c8ec381daa00b88a539Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-89485b49a32afa256bdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-4918000000-df3152da1740bcb45d3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-c9e67703b1ef9ca4f8ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-b9d2971c377f79dd6238Spectrum
MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51dSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Platelet
  • Skeletal Muscle
Normal Concentrations
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
UrineDetected and Quantified5.298 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
Abnormal Concentrations
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12310
Phenol Explorer Compound IDNot Available
FooDB IDFDB001114
KNApSAcK IDC00001152
Chemspider ID7149
KEGG Compound IDC01083
BiGG ID36774
Wikipedia LinkTrehalose
PubChem Compound7427
PDB IDNot Available
ChEBI ID16551
Food Biomarker OntologyNot Available
MarkerDB ID
Synthesis ReferenceMurao, Sawao; Nagano, Hiroto; Ogura, Sei; Nishino, Toyokazu. Enzymic synthesis of trehalose from maltose. Agricultural and Biological Chemistry (1985), 49(7), 2113-18.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yoshioka S, Aso Y: A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res. 2005 Aug;22(8):1358-64. Epub 2005 Aug 3. [PubMed:16078146 ]
  2. Guo N, Puhlev I, Brown DR, Mansbridge J, Levine F: Trehalose expression confers desiccation tolerance on human cells. Nat Biotechnol. 2000 Feb;18(2):168-71. [PubMed:10657122 ]
  3. Nie Y, de Pablo JJ, Palecek SP: Platelet cryopreservation using a trehalose and phosphate formulation. Biotechnol Bioeng. 2005 Oct 5;92(1):79-90. [PubMed:15937943 ]
  4. Fujita Y, Naka T, Doi T, Yano I: Direct molecular mass determination of trehalose monomycolate from 11 species of mycobacteria by MALDI-TOF mass spectrometry. Microbiology. 2005 May;151(Pt 5):1443-52. [PubMed:15870454 ]
  5. Lu FQ, Liu JH, Ouyang XL, Li XJ, Zhou J, Zhuang Y: [Process of human platelets loaded with rehalose before lyophilization]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006 Feb;14(1):156-61. [PubMed:16584614 ]
  6. Shirkhanzadeh M: Microneedles coated with porous calcium phosphate ceramics: effective vehicles for transdermal delivery of solid trehalose. J Mater Sci Mater Med. 2005 Jan;16(1):37-45. [PubMed:15754142 ]
  7. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
  8. Eroglu A, Russo MJ, Bieganski R, Fowler A, Cheley S, Bayley H, Toner M: Intracellular trehalose improves the survival of cryopreserved mammalian cells. Nat Biotechnol. 2000 Feb;18(2):163-7. [PubMed:10657121 ]
  9. Arguelles JC, Rodriguez T, Alvarez-Peral FJ: Trehalose hydrolysis is not required for human serum-induced dimorphic transition in Candida albicans: evidence from a tps1/tps1 mutant deficient in trehalose synthesis. Res Microbiol. 1999 Oct;150(8):521-9. [PubMed:10577485 ]
  10. Corning BF, Murphy JC, Fox JG: Group G streptococcal lymphadenitis in rats. J Clin Microbiol. 1991 Dec;29(12):2720-3. [PubMed:1757539 ]
  11. Davies JE, Sarkar S, Rubinsztein DC: Trehalose reduces aggregate formation and delays pathology in a transgenic mouse model of oculopharyngeal muscular dystrophy. Hum Mol Genet. 2006 Jan 1;15(1):23-31. Epub 2005 Nov 25. [PubMed:16311254 ]
  12. Ma X, Jamil K, Macrae TH, Clegg JS, Russell JM, Villeneuve TS, Euloth M, Sun Y, Crowe JH, Tablin F, Oliver AE: A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells. Cryobiology. 2005 Aug;51(1):15-28. [PubMed:15963489 ]
  13. Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
  14. Alcoba-Florez J, Mendez-Alvarez S, Cano J, Guarro J, Perez-Roth E, del Pilar Arevalo M: Phenotypic and molecular characterization of Candida nivariensis sp. nov., a possible new opportunistic fungus. J Clin Microbiol. 2005 Aug;43(8):4107-11. [PubMed:16081957 ]
  15. Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ: Mechanism of protein stabilization by sugars during freeze-drying and storage: native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci. 2005 Jul;94(7):1427-44. [PubMed:15920775 ]
  16. Sasnoor LM, Kale VP, Limaye LS: A combination of catalase and trehalose as additives to conventional freezing medium results in improved cryoprotection of human hematopoietic cells with reference to in vitro migration and adhesion properties. Transfusion. 2005 Apr;45(4):622-33. [PubMed:15819685 ]
  17. Alvarez-Peral FJ, Arguelles JC: Changes in external trehalase activity during human serum-induced dimorphic transition in Candida albicans. Res Microbiol. 2000 Dec;151(10):837-43. [PubMed:11191809 ]
  18. Berlutti F, Thaller MC, Dainelli B, Pezzi R: T-mod pathway, a reduced sequence for identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1989 Jul;27(7):1646-9. [PubMed:2768451 ]
  19. Kandror O, DeLeon A, Goldberg AL: Trehalose synthesis is induced upon exposure of Escherichia coli to cold and is essential for viability at low temperatures. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9727-32. Epub 2002 Jul 8. [PubMed:12105274 ]
  20. Habe H, Sato S, Morita T, Fukuoka T, Kirimura K, Kitamoto D: Bacterial production of short-chain organic acids and trehalose from levulinic acid: a potential cellulose-derived building block as a feedstock for microbial production. Bioresour Technol. 2015 Feb;177:381-6. doi: 10.1016/j.biortech.2014.11.048. Epub 2014 Nov 18. [PubMed:25479689 ]


General function:
Involved in catalytic activity
Specific function:
Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:
Uniprot ID:
Molecular weight:
Trehalose + Water → D-Glucose + alpha-D-Glucosedetails
Trehalose + Water → D-Glucosedetails